Triethylamine → HCID 58551215, compound

HRID 1908162Notes

Reaction equation

HRID 1908162 reaction equation
[CH2:1]([C:3]1[CH:30]=[CH:29][C:6]([C:7]([N:9]2[CH2:14][CH2:13][C:12]3([O:19][C:18]4[CH:20]=[C:21]([CH:24]=O)[CH:22]=[CH:23][C:17]=4[N:16]4[CH:26]=[CH:27][CH:28]=[C:15]34)[CH2:11][CH2:10]2)=[O:8])=[CH:5][C:4]=1[O:31][CH3:32])[CH3:2].C[CH2:34][N:35](CC)[CH2:36]C>CN(C=O)C>[CH3:34][N:35]([CH2:24][C:21]1[CH:22]=[CH:23][C:17]2[N:16]3[CH:26]=[CH:27][CH:28]=[C:15]3[C:12]3([CH2:13][CH2:14][N:9]([C:7]([C:6]4[CH:29]=[CH:30][C:3]([CH2:1][CH3:2])=[C:4]([O:31][CH3:32])[CH:5]=4)=[O:8])[CH2:10][CH2:11]3)[O:19][C:18]=2[CH:20]=1)[CH3:36]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 58551190HCID 58551190, compound

Product 1

HCID 58551215HCID 58551215, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1′-(4-ethyl-3-methoxybenzoyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-7-carbaldehyde (88 mg, 0.20 mmol) N,N-dimethylamine hydrochloride (83 mg, 1.0 mmol), Et3N (140 μL, 1.0 mmol) and NaHB(OAc)3 (130 mg, 0.60 mmol) in DMF (1 mL) was stirred at room temperature overnight. The reaction mixture was filtered and purified by reverse phase LC-MS (10-99% CH3CN/H2O) to yield (7-((dimethylamino)methyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)(4-ethyl-3-methoxyphenyl)methanone. ESI-MS m/z calc. 459.6. found 460.5 (M+1)+; Retention time: 1.40 minutes (3 min run).

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompurified by reverse phase LC-MS (10-99% CH3CN/H2O)

Sources & evidence

ORD record
ord-db341d295da7459991bc61f282cd99b6
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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